Vacation rentals in Chicago

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Top-rated holiday rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Guest suite in Chicago
Bike the Lakefront from a Sleek Urban Retreat
Cook in a stainless-steel kitchen with granite countertops, gleaming utensils, and a well-stocked fridge. Black and gray accents and dark woods offset a muted palette at this open-concept home. Thoughtful details include 800-thread-count linens. A retreat designed to evoke relaxation through luxury and elements of the earth. Lush bath linens & robes, luxury body and hair care products, coupled with sleek design creates a spa bathroom retreat you're sure to enjoy. Full granite and stainless steel kitchen, with wine fridge, stocked with morning essentials and Bronzeville BNB staples to ease you into the day's adventure. Relax or be social in the open space living and dining area equipped with Amazon entertainment system and Wi-Fi providing up-to-date weather, sports, news, the latest movies and yes...sometimes...work. Retreat to one of three sleeping accommodations, each drept in 800 thread count, 100% cotton linens. You'll find Bronzeville BNB thoughtful touches around every corner. Enjoy! You'll have access to the full suite including open floor plan living room/dining room/kitchen, spa bathroom, bedroom with walk in closet, hall closet, rear mud room containing washer/dryer, mop/broom, garbage tray, and fire extinguisher. There is concrete patios at the front and the rear entrances also. The backyard, main property deck and garage are restricted areas. The suite is nestled in the historic Bronzeville-Hyde Park neighborhood. Rent a Divvy bike to explore the 18-mile lakefront recreation trail close by. Chicago’s main attractions are a short drive away. The most efficient way to get around the city is UBER offering door-to-door service to all of Chicago's top attractions. Claim your FREE Uber ride (up to $5) gift from the host by signing up using this link: https://www.uber.com/invite/zkyf4 Divvy bike rentals are an awesome way to explore Chicago's 18 mile lakefront trail. The Divvy Explorer Pass includes 24 hours of bike access, with unlimited trips up to 3 hours each for $15/day. Pick up and return bikes at the 575+ Chicago & Evanston Divvy stations. Download the Divvy app for station locations and ride pass purchases. Your safety is important. Please be safe and aware of your surroundings. In any huge city, things can happen. It is suggested to not walk at night, avoid public transportation outside of downtown, and use rideshare transportation apps to avoid exchanging currency.
20–27 Dec
$252 NZD per night
4.93 out of 5 average rating, 168 reviews
Guest favourite
Guest suite in Chicago
Private Lincoln Square one bed+bath studio apt.
Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336
2–9 Sep
$302 NZD per night
5.0 out of 5 average rating, 290 reviews
Guest favourite
Apartment in Chicago
Cozy loft in Chicago's Uptown
Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; small family on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. New!Andersonville, recently voted the coolest neighborhood in US (Timeout’s survey) is only a 15-minute stroll. The CTA's Red Line/Wilson station is 3 blocks away. Overnight street-parking decals also available for guests.
6–13 Sep
$227 NZD per night
4.97 out of 5 average rating, 260 reviews

Popular amenities for Chicago holiday rentals

Stay near Chicago's top sights

Millennium Park1,243 locals recommend
O'Hare International Airport122 locals recommend
Lincoln Park175 locals recommend
Grant Park332 locals recommend
Shedd Aquarium673 locals recommend
Magnificent Mile597 locals recommend

Other great holiday rentals in Chicago

Guest favourite
Apartment in Lincoln Square
Bright family-friendly Lincoln Square 2-bed 1-bath
29 Nov – 6 Dec
$279 NZD per night
4.96 out of 5 average rating, 313 reviews
Guest favourite
Guesthouse in Edgewater
Cozy Coach House
19–26 Aug
$237 NZD per night
4.95 out of 5 average rating, 362 reviews
Guest favourite
Guest suite in Lincoln Square
Private Lincoln Square Garden Apt
19–26 Sep
$223 NZD per night
4.92 out of 5 average rating, 400 reviews
Guest favourite
Apartment in Roscoe Village
Roscoe Village One Bed Lux Apartment Near Wrigley
11–18 Sep
$249 NZD per night
4.96 out of 5 average rating, 236 reviews
Guest favourite
Guesthouse in Andersonville
Private, Charming, Coach House Loft in Andersonville
12–19 Nov
$330 NZD per night
4.91 out of 5 average rating, 338 reviews
Guest favourite
Apartment in Wrigleyville
A Novel Situation at Wrigley
19–26 Jan
$293 NZD per night
4.9 out of 5 average rating, 162 reviews
Guest favourite
Apartment in Logan Square
Cozy Private Coach House
10–17 Apr
$289 NZD per night
4.93 out of 5 average rating, 206 reviews
Guest favourite
Apartment in Logan Square
Logan Square 2nd Floor Chicago Victorian
31 Dec – 7 Jan
$238 NZD per night
4.96 out of 5 average rating, 252 reviews
Guest favourite
Home in Chicago
Wrigleyville Southport Studio
27 Oct – 3 Nov
$339 NZD per night
4.98 out of 5 average rating, 201 reviews
Guest favourite
Guest suite in Chicago
Comfortable & Cozy in Bridgeport
4–11 Sep
$173 NZD per night
4.94 out of 5 average rating, 117 reviews
Guest favourite
Guest suite in Avondale
Logan Square Garden Suite
27 Mar – 3 Apr
$201 NZD per night
4.93 out of 5 average rating, 42 reviews
Superhost
Apartment in Chicago
McCormick Place Studio/parking/sleeps up to 4
11–18 Feb
$183 NZD per night
4.81 out of 5 average rating, 58 reviews

Quick stats about holiday rentals in Chicago

Total rentals

11K properties

Rentals with dedicated workspaces

6.6K properties have a dedicated workspace

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

3.3K properties allow pets

Family-friendly rentals

5K properties are a good fit for families

Total number of reviews

476K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago